Startup Foundations

Cheryl Contee is an entrepreneur, investor, writer, founder of a digital marketing agency Do Big Things, and currently the CEO of the Impact Seat Foundation, an organization that aims to level the playing field for women of color who want to become successful business leaders. Over the course of her career, Cheryl was also successful in building Attentive.ly, a social listening and marketing automation startup focused on developing tools for non-profits.

In our conversation, we discuss Cheryl’s work with Attentive.ly, and how she co-founded the company as a spin-off of her digital marketing company Do Big Things. We talk about the market for building tools for non-profit organizations and how Cheryl has built the company over the years and eventually exited to Blackbaud in 2016.

We also dig deeper into the evolution of the startup funding ecosystem, and its many flaws and shortcomings. Particularly lack of support for female founders and founders of color. Cheryl recalls her first fundraising experiences and shares interesting insights into why the VC world isn’t willing to fund diverse founders.

Cheryl also shares the mission of the Impact Seat Foundation, and how it's trying to democratize business leadership and make it more accessible to women of color.

Sahin Boydas is a serial entrepreneur, born in the US, grew up in Turkey, who most recently founded RemoteTeam, a startup building software for remote hiring and international payroll. RemoteTeam was acquired by Gusto back in 2021, and at the moment Sahin is Gusto’s head of RemoteTeam.

In our conversation we discuss Sahin’s entrepreneurial background, and his rich experience in finding the right ideas, building good products, and then exiting successfuly. Sahin shares the insights that made him start RemoteTeam back in 2019, just before the beginning of pandemic.

We also discuss how partnerships can turn into acquisitions, the aftermath of exiting RemoteTeam to Gusto, and why Sahin decided to work for someone, for the first time in his entrepreneurial career.

Sahin also speaks on growing and selling multiple business back when he was living in Turkey, his early days in the Silicon Valley, and he shares tips on hiring and fundraising for early startups.

Jess Lee is the founder and CEO of Bitesize, a startup helping car dealerships communicate with thousands of customers at once. Jess is also an active angel investor working with the Hustle Fund.

In our conversation, we talk about how Jess got the idea to build texting tools through immigrant activism at college, and how she ended up translating her experience to a completely different space, which is the automotive industry.

Jess discusses why she decided to build software for car dealerships and what’s the business rationale behind Bitesize. She also shares why she decided to go it alone and grow her company as a solo founder. We talk about the pros and cons of being a solo founder and why investors are more likely to fund startups with multiple founders.

We also discuss how the industry has changed over the last couple of years with regard to female founders and women working in venture capital firms.

Jess also takes us back to the early days of Bitesize and shares how she got her first customer literally driving around car dealerships with coffee and donuts.

Ahmad Ibrahim is the co-founder and CEO of neo.tax, a startup that creates tax filing and automation software that simplifies the R&D tax credit application process. Ahmad's career path included studying economics and philosophy, working as a product manager at Intuit, and launching his own accounting firms.

We discuss how studying philosophy can be helpful in a career of a founder and lessons learned from Ibrahim’s first startup, Unleash. We also discuss how building an software product for accountant within the confines of Intuit has influenced Ibrahim’s will to pursue another startup venture in that space.

Ibrahim speaks on the predicament of accounting, shares his “lightbulb moment” that gave him the idea that he turned into neo.tax. Ibrahim also talks to us about the challenges of building tax automation software, his co-founders and their role distribution, and the future of legal and accounting services.

Viola Llewellyn is the president and co-founder of Ovamba Solutions, a fintech startup working on financing products for the trade and commodities sectors in Africa and other developing markets. Ovamba works as an ecosystem that helps African businesses with short-term financing and enables sharia-compliant funding structures.

We discuss the origin story of Ovamba, how it got its first users and funding, and the meeting of its co-founders - Viola and Marvin Cole. Viola shares her valuable insights into the intricacies of financing the commodities market in Africa and building unique data sets that are based on inventory and asset movement in relation to people.

We also talk about who the customers of Ovamba are - from banks in Africa to international institutions looking to finance projects on the continent. Viola shares her plans for the future of Ovamba, including possible expansion to other regions like the Middle East or Latin America.

Viola and Greg speak on the importance of blockchain technology, tokenization, and cryptocurrency in streamlining the growth and movement of assets and commodities in emerging markets. Viola also shares her thoughts on the situation of black female entrepreneurs and on making the startup ecosystem more inclusive.

Kiwi Camara is the CEO and co-founder of DISCO, a publicly traded legal tech company providing cloud-native, AI-powered solutions that simplify ediscovery, case management, and legal document review for law firms and enterprises. Kiwi’s extensive background includes a B.S. in computer science, as well as J.D. from Harvard Law School and Ph.D. in economics from Stanford.

We discuss what is DISCO, and how lawyers can use it to streamline their work with legal documents and case files. Kiwi also shares how he got the idea to start his own company and what it takes to innovate in the legal space. He also shares how he grew DISCO, from receiving the first check from investors to IPO in 2021.

We talk about the business rationale behind DISCO and why law firms adopt these types of legal solutions. Kiwi also shares his thoughts on other innovative and promising companies in the space.

Lisa Gelobter is the CEO and co-founder of tEQuitable, an independent, confidential platform helping companies address issues of bias, discrimination and harassment in the workplace.

Lisa expansive background includes working on groundbreaking multimedia projects like Shockwave, Hulu, Viacom, and serving as Chief Digital Service Officer for the US Department of Education during the presidency of Barack Obama.

Lisa talked to us about her current company tEQuitable, its mission, and how technology can be used to mitigate issues of harassment and discrimination in a workplace. We talk about different types of organizations tEQuitable has already worked with, and how it tackles complex issues like equitable workplace in the era of a fully remote work.

Lisa also shares what made her pursue the idea of building a startup, and shares her thoughts on the issue of inclusivity and diversity of funding in the world of venture capital and startups. We also discuss the issue of upward mobility among immigrants and minorities in the US. Lisa also shares some insights on building a diverse and friendly workplace from the very beginning.

Henrik Werdelin is a serial entrepreneur and author, who co-founded BarkBox, a subscription-based service providing a monthly box of treats and toys for dogs. BarkBox is now called BARK and it is a publicly traded company, after its IPO in June of 2021. Henrik has also started Prehype, a collective of entrepreneurs that builds products and companies through collaboration with corporations and VCs.

Henrik talks to us about the early days of BARK, randomly meeting his co-founder Matt Meeker during a cruise ship and the strategies used for growing their company. We discuss the creative marketing and the famous 4/20 campaign, as well as raising capital at the beginning of the twenty-tens.

We also talk about the best dog breed for founders and delve deeper into the world of pet startups. Henrik speaks on his book “The Acorn Method”, which covers building new product lines within the confines of an existing business. and shares interesting insights on what makes a good startup employee and how the roles of early employees shape across the lifespan of a company.

Courtney Caldwell is the co-founder and COO of ShearShare, a “Hairbnb” startup that helps salon owners maximize their earnings potential by renting out their spaces to beauty industry professionals.

Courtney talked to us about how ShearShare works, and why “space as a service” has been such a big deal for people working in the beauty industry. We also go over why many professionals in the space have been deciding to pursue a solo career, instead of working as employees in salons.

We cover the origin story of ShearShare, which is rather far from serendipitous. Courtney herself was a high-ranking employee at Oracle, while her co-founder and husband has been one of the most notorious barbers and beauty industry professionals in the country. After finding a niche neglected by tech, they’ve initially bootstrapped the company before going through 500 Startups and receiving first investor check.

We also discuss the bias against married founders in the VC community, and how limited that industry still is in terms of funding initiatives that make a difference for people in need.

Courtney also speaks about interesting companies to watch in the beauty space and talks about what the future may hold for the entire industry.

Nial DeMena is the CEO and co-founder of Vella Bioscience, a femtech startup dedicated to sexually empowering every woman. Vella’s flagship product is a pre-play topical serum designed to help women achieve better orgasms, no matter their hormonal status.

We talked to Nial about the details of how Vella’s main product works and what’s it like doing business at the intersection of sexual wellness and femtech industries. Nials also shares the rationale behind Vella’s multichannel distribution strategy, which involves direct-to-consumer and retail.

Nial shares more information about his background and previous ventures, including starting multiple health tech companies (Temescal Wellness and Manna Molecular Science). He also speaks more about the research that went into creating their product and how scientific discoveries about CBD and cannabinoids turned into the actual production of the serum.

Nial also gives us valuable insights regarding the regulatory issues in the sexual wellness space and how studying the therapeutical potential of cannabinoids can shape the future of Vella’s products.